In the aftermath of Charlottesville, shortly after Donald Trump absolutely spooned his denunciation of neo-Nazis, something small but extremely significant happened.

Almost immediately after he claimed that there was violence “on both sides” and that the alt-right contained some “very fine people”, charities and non-profits began cancelling their annual galas at Mar-A-Lago. The American Cancer Society, the American Red Cross, the Salvation Army – organisations which, presumably, were happy to turn a blind eye to the Muslim travel ban, the trans military purge, the Russia investigation, the Mexicans-are-rapists-and-murderers routine – suddenly all felt that the KKK-konnection was perhaps a little too much, and so made alternate arrangements.

Within the week, at least 16 different organisations had cancelled proposed fundraisers and had taken their hire fees with them – potentially costing Mar-A-Lago (and, by extension, Trump) about $4.4m in lost bookings.

Tucked in among the list of cancellations was one organisation that really caught our eye: Leaders In Furthering Education (LIFE).

LIFE’s founder and chairwoman gave a full-throated unequivocal statement saying that “anyone who would demonstrate even a modicum of support for [neo-Nazis] by insisting that there are ‘good people’ among them is not deserving of my personal patronage or that of my foundations […] Therefore, I am recommending to my board that we move this year’s gala from the Mar-A-Lago Club.”

There’s a reason why LIFE turning its back on Trump is more significant than some of the better-known, big-name organisations like the Red Cross or the Sally Army doing the same.

The short version is: LIFE has held annual galas at Mar-A-Lago for 24 years. Its founder is a self-proclaimed Trump loyalist. She is a close personal friend of the family, has been a member of Mar-A-Lago for decades, and even goes so far as to eat her Thanksgiving dinner there. She is precisely the sort of person you’d have expected to stay onside with Trump until the bitter, bitter end.

As always though, there is a little more to it than just that – and in order to explain why this seemingly tiny incident, this relatively minor hiccup, could actually prove to be catastrophically bad for Donald Trump we need to tell you a longer, more complicated story: the story of American Media, Inc.

American Media, Inc. is the publisher behind a number of downmarket weekly tabloids in the States. The sort of cheap, celebrity-focused gossip mags that sit at the checkouts of American supermarkets. The ones that are continually blasting film stars for getting fat, or developing cancer, or divorcing Jennifer Aniston.

They are widely derided for being lowbrow, sensationalist trash – but the history of American Media, Inc. is anything but. It spans sixty years and takes in everything from the Mafia, McCarthyism, Russian espionage and Rupert Murdoch, to anthrax attacks, the death of Elvis Presley, Pulitzer Prize winning plays, and high-profile staffers of practically every American administration from Truman through to Trump (often including the presidents themselves).

We’re going to try to tell you that story, as best we can, in four parts.

In doing so, we should be able to demonstrate not only why LIFE’s decision to pull their plans at Mar-A-Lago should be concerning to Trump, we should also be able to shed a bit of light on some of the more pressing questions of the current media landscape.

Part I/ The Tabloid Triangle

To start with, we’ll take a look at the beginnings of American Media, Inc.’s flagship title, the National Enquirer. As we do, we’ll also explain how mafia money, mob mentality and the attempted assassination of one of New York’s most notorious crime bosses in the 1950s created the tabloid magazine boom in 1970s Florida.

Part II/ Angels and Un-American Activity

Aside from its mob connections, the National Enquirer also had a high-ranking political powerbroker lurking in its shadows. Lending the Enquirer an air of legitimacy was McCarthy’s right hand man through the Red Scare of the 50s, Trump’s lawyer through the discrimination suits of the 70s, and an incorrigible gossip throughout – Roy Cohn.

Part III/ Suburban Decay

The National Enquirer‘s breakout in the 60s and 70s inspired a number of imitators to horn in on the market– with Rupert Murdoch, the New York Times, Time and others all trying snatch up its space on the shelves. But when American Media, Inc. came to town, competition quickly turned to collaboration. And with their powers combined under David J Pecker, the supermarket tabloid suddenly became a serious and substantial force.

Part IV/ Electile Dysfunction

The National Enquirer broke the habit of its lifetime in the 2016 election by endorsing a candidate for president. Unlike almost every other publication in the rest of America, the Enquirer endorsed Donald Trump. Was that because – as most people assumed – the CEO of American Media Inc just so happens to be a close personal friend of Donald Trump’s? Or was there something else at play?

2019 BONUS

Part V/ No Stone Left Unturned

With Michael Cohen headed to the Big House and Roger Stone now in cuffs, we thought it was high time we revisited our series on the National Enquirer to catch up with some of our old favourites and see how they’re all getting on. Here’s three more tales of tawdry tabloid gossip that have somehow turned into internationally significant affairs…